Bash Bish Falls is the highest waterfall in the state, located in the Taconic Mountains of southwestern Massachusetts. The falls are made up of a series of cascades, nearly 200 feet in total. The falls are made up of a series of cascades, nearly 200 feet in total. Photo by Escape Brooklyn
EB’s Berkshires Top 5:
• Art at MASS MoCA: Set inside a massive 19th-century factory complex, MASS MoCA is one of the country’s most ambitious contemporary art museums. Plan at least half a day to wander through immersive installations by artists like James Turrell and Sol LeWitt, plus sculpture-filled courtyards and performance spaces.
• Tacos & Natural Wine at Casita: At the entrance to MASS MoCA, this stylish counter-service spot offers daytime breakfast and coffee, then transitions to tacos, ceviche, and natural wine in the evening. A standout for quick, beautiful plates before or after the museum.
• Exploring Greylock Works: This sprawling former textile mill in North Adams has been reimagined as a creative campus—home to events, maker studios, and an evolving food and drink scene. Check the calendar for public happenings, from seasonal markets to chef pop-ups and vintage fairs.
• Hiking the Hickey and Peeskawso Peak Loop at Monument Mountain: This scenic 2.5-mile loop near Great Barrington offers a moderately challenging climb with rewarding views from Peeskawso Peak. The rocky summit overlooks the Housatonic River Valley and Taconic and Catskill ranges beyond—especially stunning in early autumn.
• Dinner at The Dream Away Lodge: Deep in the woods of Becket, this eccentric 200-year-old farmhouse hosts one of the region’s most atmospheric dinners. Expect comfort food classics, vintage lighting, and live music—sometimes planned, sometimes spontaneous. It’s part roadhouse, part salon, and completely unforgettable.
Just over three hours from New York City, the Berkshires offer a scenic and low-key alternative to more crowded Upstate destinations. Nestled in western Massachusetts near the New York border, this stretch of rolling hills, dense forests, and storybook towns makes an ideal long weekend escape—especially in early autumn, when the air cools and the region’s hardwood forests begin to turn.
The area blends pastoral charm with a strong creative undercurrent: historic inns and roadside motels coexist with experimental restaurants, performance spaces, and forward-thinking farm stands. Home to some of the Northeast’s best foliage and a bounty of trails, the Berkshires are a haven for hikers, design-minded travelers, and anyone craving a slower pace.
Read on for our guide to the area, with our picks for the best outdoor attractions, arts/culture picks, dining and lodging.
What to Do in the Berkshires: Get Outdoors + Visit the Country’s Largest Contemporary Art Museum
Photo: Escape Brooklyn
Visit MASS MoCA
Located in a vast 19th-century mill complex, MASS MoCA is one of the country’s largest contemporary art institutions, known for its monumental exhibitions, immersive installations, and dynamic performance programming. The museum’s campus spans multiple buildings and outdoor spaces, with long-term works by James Turrell, Sol LeWitt, and Laurie Anderson alongside rotating exhibitions and live events. A cultural anchor for North Adams, it’s well worth the detour north for anyone exploring the region.
Hiking the Berkshires: 3 Favorite Trails
The Berkshires offer some of the most scenic hikes in the Northeast, with options ranging from quick forest walks to sweeping summit climbs. Monument Mountain, just outside Great Barrington, is a local favorite with a moderate loop trail and panoramic views across the valley. Bash Bish Falls—Massachusetts’ tallest waterfall—requires only a short stroll to reach its dramatic cascade. For something more atmospheric, Ice Glen in Stockbridge winds through a glacial ravine dotted with moss-covered boulders and towering pines, staying cool even in summer.
Drive Route 7
The scenic stretch of Route 7 between Stockbridge and Sheffield is one of the best leaf-peeping routes in the Northeast. Plan to make frequent stops—farm stands, old barns, panoramic vistas, and fields full of goats and sheep are around nearly every bend. Local eggs, heirloom tomatoes, cheeses, and jams make great souvenirs (or dinner ingredients back in the city).
Where to Eat + Drink: the Best Restaurants + Bars in the Berkshires
Photo: the storied Dream Away Lodge bar, found in the woods near Becket, MA. Photo: Jeff Fay
Mezze Bistro + Bar – Williamstown, MA
Known for its contemporary farm-to-table menu, Mezze Bistro + Bar offers seasonal dishes crafted from locally sourced ingredients. The restaurant’s commitment to sustainability and flavor makes it a standout dining experience in the northern Berkshires.
Once Upon a Table – Stockbridge, MA
This intimate eatery focuses on modern American fare with a farm-to-table approach. Menus change frequently based on seasonal availability, ensuring fresh and inventive dishes in a cozy setting.
Dottie’s Coffee Lounge – Pittsfield, MA
A vibrant spot for coffee enthusiasts, Dottie’s offers strong brews and a menu of classic options with a twist, such as grilled cheese sandwiches fried in ghee. The lounge also hosts live music during its popular Domingo Brunch on Sundays.
Dorothy’s Estaminet – Pittsfield, MA
Adjacent to Dottie’s, Dorothy’s Estaminet provides a more refined dining experience with platters for two and a selection of seasonal cocktails, all served in an elegant setting.
State Food and Drink – North Adams, MA
Located at Greylock Works, this event-driven restaurant offers a diverse menu that includes Southern cuisine on “Blue Mondays” and Vietnamese dishes on Tuesdays. Weekend brunch and dinner feature farm-to-table fare, making it a dynamic dining destination.
Casita – North Adams, MA
Situated at the entrance of MASS MoCA, Casita serves a variety of dishes ranging from chilaquiles during the day to tacos and ceviche in the evening, providing a flavorful experience for museum-goers and food lovers alike. Mezcal cocktails are a specialty; the local favorite is the hamburguesa. Save room for churros!
The Dream Away Lodge – Becket, MA
Tucked deep in the woods of Becket, The Dream Away Lodge is a one-of-a-kind destination where dinner feels like a performance and the atmosphere is half the experience. Housed in a 200-year-old farmhouse, the space blends roadhouse eccentricity with old-school supper club energy: think string lights, velvet drapes, and a piano in the corner. The kitchen turns out seasonal, locally sourced comfort food, while the bar hosts an ever-rotating lineup of live music, readings, and events. It’s as much a gathering place for the creative community as it is a restaurant — plan to linger.
